Moments Like This
by LightLeadingMe
Summary: Continuations and variations of the many Jack and Karen moments throughout the series. Rated T for now
1. Coffee and Commitment

**_Coffee & Commitment - Season 3, Episode 11_**

 _"We can get our minds off of things by touching each other inappropriately."_

 _"Good idea."_

It was ten minutes later and Will and Grace were making some sort of love declaration in the middle of the wedding ceremony and Karen was about to snap. She needed alcohol and she needed it now. Beside her, Jack wasn't doing so well either. She had her hand in his lap, her fingers dangerously close to his crotch and he had an arm wrapped around her, his hand brushing her left breast under her jacket. The distraction was nice, but it wasn't enough.

Karen turned her head and whispered to Jack quietly as Will and Grace finally sat back down so the ceremony could continue. "Meet me in the coat closet in five minutes." With that, she stood and ran down the corridor to the coffee bar. She snatched a cold espresso off the cart and slammed it back, missing the familiar taste of Bailey's with sore hopelessness. She then took off for the coat closet at the end of the hall and walked in, not bothering to flip on the light above her head.

Not a minute later, Jack strolled in, closing the door behind him. "Karen?"

Karen surged forward out of the darkness of the closet and grabbed Jack by the back of his neck, bringing him roughly down to her mouth. He stumbled a bit into her, his hands grasping at her hips to steady himself. She could feel him try to pull away, most likely about to question her, so she pressed her tongue against his lips, knowing he would taste the coffee on her breath.

Jack suddenly stopped struggling and moaned loudly, his mouth opening to seek out Karen's dark roast flavored tongue, but Karen resisted, pulling her mouth away just far enough so he couldn't touch her tongue. Understanding that she was trying to distract them both, her sexually and him with a teasing amount of caffeine, he smoothed his hands down to her ass, squeezing it until Karen whimpered against his mouth.

Never parting their lips, Karen shrugged out of her jacket, leaving her in her strapless shirt and matching pants. She grabbed one of Jack's hands from her rear and brought it to her chest, groaning appreciatively when he began to knead breast. Finally feeling the need for alcohol slip away and become replaced with a need for sexual release, Karen opened her mouth wide and stuck her tongue out so Jack could finally get his caffeine fix. She expected him to just tangle his tongue with hers like they usually do when they makeout, but instead she felt his lips wrap around her muscle and begin to greedily suck on it like a lollipop. Karen went weak in the knees at the new sensation and the remaining thoughts of alcohol flew out of her head and were replaced with a throbbing between her legs.

The sound of raucous cheers and hollers suddenly sounded from down the hall and the couple parted in surprise. Their heavy breaths filled the small room and they stared in the direction of each other, not really able to read one another's facial expressions in the darkened closet.

"I guess the weddings over," Jack said quietly.

Karen nodded, ignoring the fact that he couldn't see the movement. "We better get out of here, honey. The quicker they cut the cake, the quicker we leave, and the quicker I get home to my Jack Daniel's on the rocks."

In the midst of the cutting of the cake, Karen found one of the grooms' sister and luckily the woman was so drunk she didn't even bat an eye at giving Karen half the contents of her flask. Jack found a new boy toy to smoke with, creating yet another habit to counteract his caffeine obsession. Karen shook her head and sighed as she watched him shamelessly flirt whilst trying not to cough as the unfamiliar feeling of smoke filled his lungs. She looked down at her drink and tossed the remaining contents back, hoping it was enough to satisfy her for the drive home. The makeout session was enough to distract her earlier, but the second the alcohol from the flask touched her lips her sex drive dwindled down drastically, replaced with a euphoria of familiarity and dulling senses.

Karen tossed the empty cup behind her, careless as to where it landed and looked back over at Jack just as he glanced away from his smoking companion. Their eyes met and Karen felt the rush of desire coarse through her body and settle right back between her legs.

"Shit."


	2. It's the Gay Pumpkin, Charlie Brown

**_It's the Gay Pumpkin, Charlie Brown_ \- Season 5, Episode 5**

"Telllll me somethin' gooood..." Karen slurred, stumbling around Jack's apartment in a drunken stupor. "I'll tell you something good, Stanley Walker!" She raised the bottle of bourbon to her lips and swigged some back before throwing the almost empty bottle on the ground, smashing it into tiny pieces all over the living room floor. "Oh no," she whispered, collapsing to the ground to clean it and salvage the last of her liquor.

Hearing the commotion from the bathroom, Jack quickly emerged from the shower and wrapped a towel around his wet body. He ran into the living room to find Karen on her hands and knees, trying to pick up the broken shards. "Karen, what happened?" He rushed over to her, minding the glass and his bare feet. He grabbed her arm to help her up, but she shoved him off roughly.

"I'm fine!" she yelled. " _Don't_ touch me." Jack watched as she sat back on her heels for a moment looking as if she were trying to catch her bearings. "I gave that man everything," Karen hissed. "He told me to sleep with other people because he was _fucking_ _her_! I was faithful. I'm mean I almost, but I... I _waited-_ " Her voice cracked as she trailed off and she let out a heart wrenching sob.

Jack crouched down and lifted her up from the floor, his heart breaking for his best friend. He wrapped his arms around her waist and kissed her shoulder as she cried into his bare chest. He wasn't sure what to do. He'd never seen Karen cry before. After she told him that she left Stan he offered her his bed for the night until she sorted things out in the morning, telling her she shouldn't be alone. She agreed and then poured another glass of bourbon. He eventually finished cleaning up _Jacque's_ and ushered her into the apartment so he could take a quick shower, promising her a night of movies and cuddling. He didn't think anything of leaving her for those short twenty minutes until he heard the bottle smashing to the ground.

"You'll get through this, Karen. You're strong, beautiful, and the bravest person I know," he whispered in her ear. "I love you, Karebear." After a few moments, her sobs died down, only small sniffles and hiccups escaping her. Jack kept his lips pressed to her ear, humming quietly as he rocked her side to side. When he felt her breathing finally slow down and match his, he kissed her ear softly. "You wanna get cleaned up?"

Karen nodded against him, but didn't move. If anything, she squeezed his neck even tighter. Jack smiled and smoothed his hands down to her bottom and then grabbed the back of her thighs, lifting her up so she could wrap her legs around his waist. He carried her to the bathroom and set her on the sink, prying her arms off him so he could turn on the shower. As the water warmed up, he grabbed a moist towelette and began wiping the makeup streaks from Karen's face as she sat idly, her eyes downcast and focusing on the tiled bathroom floor. He threw the towelette away and Karen looked up at him with bloodshot eyes.

"Thank you, Jackie," she whispered.

Jack smiled in support and nodded before he walked over to check the water by placing his hand under the stream, deciding it was warm enough. He lifted Karen from under her arms and set her back down on the floor so she was standing in front of him. He unbuttoned her shirt and tugged it down her arms, dropping it to the floor at their feet. He removed her hair piece and clip, letting her dark tresses fall down around her face and then undid her trousers, sliding them down her legs. He helped her remove her jewelry and then tentatively reached around her back to her bra, unhooking it and dropping it to the floor with the rest of her clothes.

Karen reached down to remov her own panties and swiveled around Jack to step into the shower. Jack gathered her clothes and carried them into the bedroom, tossing them in the hamper with his clothes. He went back to the living room and cleaned up the glass and mopped the floor. When he was done, he check the clock on the kitchen wall and frowned. Karen had been in the shower for a while. He entered the bathroom and his heart broke all over again. Karen was in the corner of the shower sitting down, her legs pulled up to her chest, her arms wrapped around her knees, and her cheek resting against them, staring at the wall.

Shaking his head, Jack untied the towel from around his waist and stepped into the shower with her. "Kare," he said gently to get her attention. She looked up at him in defeat and Jack knelt down in front of her, his hand cupping her cheek. "Want me to wash your hair?"

Karen nodded and they stood together. Jack grabbed his shampoo off the shelf and poured a generous amount into his hands as Karen pumped body wash onto a loufa. Jack lathered her hair with shampoo, massing it into her scalp slowly and Karen quickly washed her body. After rinsing her hair and body and repeating the process with conditioner, Jack went to turn the shower off, but Karen wrapped her arms around his waist, halting him. With their height difference, Karen's cheek rest perfectly over his heartbeat. They stood still, holding each other until they felt the water become cold. Jack turned off the shower and grabbed two fresh towels from the towel rack on the wall.

They dried off in silence and then made their way into the bedroom. He handed her a large tshirt from his drawer and slipped on some loose pajama bottoms, foregoing a shirt. They climbed into bed, Jack flipping off the lamp on the bedside table, the only light illuminating the room coming from the large window. Karen was on her back, her head turned towards the window and she stared blankly, millions of things running through her mind at once.

Jack rolled over and slipped his legs between hers, his arm draping over her stomach and his head resting upon her chest, snuggling into her bosom. He watched her as she watched the city lights. Her eyes began to flutter closed and Jack's followed suite, their breathing evening out slowly as they fell into slumber.

* * *

 **Well okay. That was a thing... Um... review?**


	3. Fred Astaire and Ginger Chicken Part 1

**_Fred Astaire and Ginger Chicken_ \- Season 6, Episode 20**

* * *

"Mmm," Jack murmured contentedly against the skin of Karen's neck. "I'm glad we're friends again, Karebear."

Karen smiled and idly rubbed his back, her eyes still closed from their nap. "Me too, Poodle."

They were lying on Jack's bed, facing each other after a long day of shopping. Jack had his nose buried in Karen's neck just below her chin that was resting on top of his hair. They were pressed as close together as they could manage, their legs slightly tangled. Karen's arms were wrapped around his shoulders and Jack's around her waist, his hand spread across the expanse of one of her butt cheeks.

They didn't start out in this position. Ever since learning a few years ago that Karen was the little spoon, Jack loved cuddling himself up to her from behind, his body almost overwhelmingly large over hers. He would slide his hand under her shirt and rest it against her flat stomach and nuzzle his nose in her hair. Karen would lay her hand atop his and wriggle her behind against his crotch, hoping to get a rise out of him. It didn't usually, but every now and again she'd feel him poking her and she would jokingly chastise him. They'd giggle for a few minutes and then eventually settle down and fall asleep. During their naps they'd shift and wake up in various positions. More often than not, Karen awoke with her head on his chest and her leg tossed over his hips. Jack was the only one of their friends that knew Karen was a complete cuddle bug.

"Do you think we'll be friends forever?" he asked randomly.

Karen let out a short chuckle. "Of course, silly. Why would you even ask that?"

Jack shifted his head back to see her face and waited until she looked down at him, their noses brushing in their close proximity. "You literally ditched me for another man yesterday."

She raised an eyebrow at him. "You ditched me for another woman."

"Cause you told me to!"

"I didn't think you'd do it!"

They stared at each other, green eyes glaring into blue, searching, until finally huge smiles broke out on their faces.

"You know I love you, Jack," she said, her eyes gleaming.

Jack's smile widened. "I know," he replied softly. "Its nice to hear it though. You never say it."

Karen furrowed her brow, surprise covering her features. "I don't?" He shook his head, his nose rubbing against hers at the movement. Karen pouted at this. She knew she wasn't the most affectionate person in the world, but she'd like to think at least the most important man in her life knew how much she cared for him. "Well, from now on I'm going to tell you every day that I love you."

"You don't have to do that-"

She closed the tiny gap between them and kissed him, cutting him off. Jack smiled against her and kissed back. She parted from him, but Jack continued to peck her lips repeatedly until Karen kissed him full on the mouth again, a little deeper this time. Seemingly satisfied, they parted finally and Karen pressed her lips against his forehead, running her fingers through his hair.

Jack snuggled himself back into her neck and squeezed her rear end in his hand causing Karen to sigh comfortably above him.

"I love you, too, Karebear."

* * *

 _ **end part 1**_


	4. Fred Astaire and Ginger Chicken Part 2

**_Fred Astaire and Ginger Chicken_ \- Season 6 Episode 20 (part 2)**

* * *

"Karen! Watch your foot!" Jack exclaimed from across the tub. "You almost kicked my _particulars_!"

Karen rolled her eyes. "Your _particulars_? What is this, 1942?"

They were in her large tub with bubbles up to their chests, Jack on one side and Karen on the other. Her hair was pinned up, without her hair piece, a martini in one hand and the remote for the stereo in the other. Jack had both arms out of the water, resting on the edges of the tub with a soothing ice mask on his eyes.

"Just be careful," he said exasperated. "I have have a date tonight and I don't want Little Jack and the Boys to be shy about seeing him because some lush beat them up."

"Sorry, honey," Karen sighed. "I just can't get comfortable." She emphasized her point by swishing around, trying to relieve the lower back pain she'd been experiencing lately. "Since Finny and I got engaged we've been doing so much more stuff that Stan and I never got to do and my back is killing me from it. You know he actually made me _walk_ to the limo the other day?" Jack looked at her and shook his head in disbelief. "I mean seriously! Who does he think I am?"

"The nerve of some people," Jack scoffed. He watched her frown and try moving around the tub again when an idea struck him. "Hey! Want me to give you a back rub?" he asked excitedly. "You loved when I gave you massages all those years ago."

Karen grinned, her eyebrows raised. "Sure, honey!" She set the martini glass on the edge of the tub and scooted herself over to him, turning around so he'd have easy access to her back. Jack leaned forward and started gently massaging her shoulders, remembering the way she liked it. Karen sighed in relief and lolled her head forward as he worked her muscles. His hands moved down the middle almost teasingly and then disappeared under the water. "Lower, honey," she instructed him. "My lower back is-" He reached the perfect spot and Karen's eyes almost rolled back into her head at his touch. "Ohhhh my God," she moaned loudly.

Jack grinned and continued to massage the stiff area, quite satisfied with himself that he was relieving her of pain. Karen flung her arms out and gripped onto the tub, throwing her head back, her moans growing louder by the minute. Jack giggled and was about to say something when the door to the bathroom flung open.

"Karen!"

"Lyle!"

"Jack!"

"Finster!"

They all stared at each other in surprise, each not knowing what to say. Finally Lyle spoke out, his face red with anger. "What the bloody hell is going on in here?!" he exclaimed.

"I'm taking a bath," Karen explained with a frown.

"With another man?!"

"No, with Jack."

"Hey!" Jack protested, crossing his arms over his chest. A pout settled on his lips and he glared between Karen and Lyle.

"Karen, you get out of that tub this instant!" Lyle demanded, his finger pointing to the spot next him.

Karen felt her own anger rise within her. "You can't tell me what to do!" she screeched at him.

"I cannot believe what I am seeing, I cannot believe what I am hearing!" Lyle shouted. "This is an outrage!" He stormed from the room and Karen rolled her eyes.

"Can you believe him?!" she asked Jack, turning her head to look at him over her shoulder.

"I know, right?" Jack sighed. "He didn't even compliment me on my mask." He took the ice mask off his face and tossed it aside while Karen stood from the tub.

"No, Jackie," she admonished him. "He thinks he can go around telling me what I can and cannot do!"

Jack tried not to stare as Karen reached for a towel, her perfect behind presented to him. He shook his head and stood up also, accepting the towel she offered. "Well, Kare," he began, wrapping the towel around his chest. "He did walk in on you with another man."

"In a completely platonic fashion!"

"Is it?" he asked, watching as she too wrapped the towel around her chest, covering her perky bosoms. "I mean, we were in a tub, naked, I was rubbing your back, you were basically screaming in pleasure... It all adds up."

Karen scoffed and stomped her foot. "It's ridiculous! You're my best friend!"

Jack softened and smiled, touching her arm gently. "Aww, Kare," he addressed her quietly. "That's so sweet." He looked to the door and frowned. "Maybe you should go talk to him, though. He seemed pretty upset."

"Maybe you're right." She scrunched up her face in annoyance. "I'll be back, honey."

She left the room and headed for her master bedroom while Jack rummaged through her cabinets for a facial mask. Finding one, he opened the jar and began applying the gel to his face, humming a tune under his breath. He paused when shouts erupted from the room next him, Karen's bedroom.

"You're being so stupid!" He heard Karen shout. "He's my best friend!"

"I don't like the way he touches you!" Lyle screamed back. "You're my fiance and I don't want you flouncing around with other men!"

"It's not flouncing, that's just the way he walks!"

Jack pouted and sat on the chaise closer to the door, desperate to hear more.

"And since when do you get to tell me what to do and who I can or cannot hang out with? Jack is the most important person in my life, you giant English moose!" Karen exclaimed. "I hung around him when I was with Stan!"

"I'm not Stan!" Lyle said to her. "I don't give a damn what your ex-husband let you do! You're mine now and you'll do as I bloody well say, woman!"

A slap sounded and Jack gasped dramatically, a hand pressed against his chest. A door slammed and seconds later, Karen appeared in the doorway of the bathroom, her face pink and her eyes clouded with animosity.

"Kare," he breathed, rushing to her side. "Are you okay?"

"Ugh, he pisses me the fuck off!" Karen shrieked. "I don't care what he thinks, I'm not sacrificing my happiness and best friend to be with that asshole!"

Jack, once again, touched, placed an arm around Karen, pressing himself into her side. "You really mean that, Karebear?" he asked tentatively.

Karen's features relaxed and she looked up at him with adoration. "I told you I love you, Jackie," she said. "I don't want another person to come between us."

Jack kissed her cheek and Karen wrapped her arms around him, squeezing tight. "Wait, Kare," Jack said, realization dawning on him. "We don't want to be Will and Grace!"

Karen let out a short laugh. "Jackie, we could never be that pathetic!"

"Then go get Lyle!" he pushed her off him and pointed to the door. "I love you, Karen, but we cannot end up like Will and Grace. You need to get your man back." He looked between them both and then at the tub. "Maybe we should cool it for a while. Let the fondle fall down on the wayside until after you guys get hitched."

"Are you sure, Poodle?" Karen asked, a pout forming on her lips. "I don't want you to feel left out again."

Jack smiled wholeheartedly at her and leaned down to press his forehead against hers. "I won't, I promise."

Karen jumped up and down and clapped. "Well, let me go catch my man! I hope he'll forgive me." She grabbed Jack's hand between hers and squeezed. "Oh, thank you, Jackie," she beamed up at him. "I'll never forget this."

Jack smiled back, a little forced if he really analyzed himself. "No problem, Kare."

She gave him a quick peck before dashing out of the bathroom and off to chase her fiance to win him back.

Jack glanced around the room and repeated all that went on in the past 15 minutes through his head. He kept settling back on the feeling that Lyle was too possessive, but wanting nothing more than for his friend to be happy, he brushed the thought aside and went to wash the mask off his face.

* * *

 **Listen guys, I'm gonna be really honest with you ... I'm super drunk. I wrote this all while drunk so I apologize wholly if not of it makes sense. Okay byeeeee**


	5. Secrets & Lays

**_Secrets & Lays_ \- Season 1, Episode 17**

 **Chapter inspired by:**

 _"Okay, and then a little over-the-sweater action, but that's it."_

 _"Grace! I got further with Jack tonight!"_

* * *

Karen emerged from the master bedroom of the cabin and strolled down the hall into the kitchen, an empty bottle of wine dangling from her fingertips. She noticed Jack sitting on the counter, eating some pretzels he must have found in the pantry. He was wearing blue pajama pants and a matching button up shirt, his feet clad in a pair of black socks and moccasin slippers.

"Hey honey," she greeted him as she set the bottle on the counter. She bent down under the sink and grabbed another bottle of wine. "Couldn't sleep?"

Jack shrugged, watching Karen open a drawer and take out a corkscrew. "Its always a little difficult to sleep someplace new. Plus the quiet is unnerving. I'm used to the hustle and bustle of the city."

Karen nodded in agreement as she popped the cork on the bottle and grabbed two glasses from the cabinet, moving about the kitchen is ease and familiarity. "Well come hang out with me, honey!" she suggested, handing him a glass and pouring a generous amount into the goblet. "Come on, we'll try on my furs and drink."

Jack hopped down from the counter in glee, almost spilling his wine. "Eee! Yay!"

Twenty minutes later, they were in Karen's expansive closet. She explained it was smaller than the one she had at home, but it wasn't like she and Stan were there for months at a time. Jack was rifling through her many furs, caressing and gushing over them fondly. He found a short fur jacket and hat, throwing them on his body and striking a pose for her. Karen tipped her wine glass and gulped the remaining down before standing from the lounge chair and prancing over to Jack.

"Hey, pick out an outfit for me, honey!" She exclaimed in excitement, holding on to his arm and pleading with her eyes. Even though she met Jack only a few months ago, she knew the second they touched stomachs at Grace's office that she had him wrapped around her little finger.

"Okay!" He replied, the ensusiasm radiating in his blue eyes, almost making them sparkle. He turned and began looking through the clothes that hung on the wall. "Hmmm," he contemplated, his eyes shifting between two pieces he knew would look gorgeous on his friend. Making a decision, he grabbed the nightie with fur straps and fur covered boots hidden in the very back of the shoe section. He handed the items to Karen with a devious look in his eyes.

"Really?" she asked, observing the items he chose.

"Please?" he pouted, flashing his baby blues and fluttering his eyelashes.

Karen quickly realized after meeting Jack that he had her wrapped around his little finger as well. Rolling her eyes, she untied the belt of her red silk robe and dropped it to the floor.

Jack's eyes widened. "Have you been naked under there this entire time?"

She wasn't completely naked; she had on a pair of black undies. Karen raised her eyebrow as she reached for the nightgown. "Yeah? You've seen me naked before." She noticed Jack trying his best not to stare at her breasts and she smirked at his obvious gaze.

"Well, I mean," he started quietly. "I've seen your ass, but not, um..."

Karen rolled her eyes again and dropped the nightie. "For Godsakes, they're just boobs!" She reached over and grabbed his hands, placing them on her breasts. "Here, feel."

Jack's eyes widened as he held Karen's boobs in his hands. He felt her nipples harden under his palms and he wasn't sure if it was from the harsh winter air outside the cabin or from him. He didn't need to know. He also didn't care because her boobs were amazing. "Wow," he breathed out.

Karen, slightly perplexed by his reaction, frowned at him. "Have you seriously never touched someone's tits before?"

He shook his head, still weighing the mounds in his hands. "I'm gay," he said nonchalantly. "I never wanted to."

"Oh," she said. "If I'm making you uncomfortable, honey-"

"No," he replied quickly, and a little too loud. He cleared his throat and shook his head. "I mean, I never wanted to touch a woman's breasts... until I met you."

Karen swallowed loud and tried to ignore the butterflies that suddenly erupted in her stomach. "Oh."

Nothing else was said for a few moments. It got awkward and heavy and they stared at each other in silence. Karen finally stepped away and Jack dropped his hands. Silently, she began dressing in the outfit he chose for her. When she was done, she spun around and struck a pose for him. "How do I look?"

Jack narrowed his eyes, assessing her attire. "Ah! The last touch!" He snatched a coat from the closet and helped her in it. "Fabulous!"

Karen grinned and danced a little in her spot while Jack admired her new look. "Hey Kare? Are you a good kisser?"

She stopped her little dance and stared up at him. "What?"

Jack swallowed loudly, realizing he just blurted that out only minutes after touching her boobs. "Sorry," he mumbled. "I was just wondering-"

"No, it's okay, honey," she assured him with a smile. "It just took me by surprise that you asked." She stepped forward so she was right in front of him. "There's only one way to find out."

Jack grinned as she reached up and wrapped her arms around his neck, one hand tangling in the hair at the back of his neck to bring him down to her while Jack wrapped his arms around her waist. She brought his face down to hers and just as she closed her eyes, her mouth inches from his, Jack pulled away. "Wait."

Karen's eyes popped open in a mix of curiosity and disappointment. "What?"

"What about your husband?" he asked.

"Are you still gay?"

"Yeah?"

"Then who cares about my husband?"

With that she brought her lips to his and kissed him. She caught his bottom lip between hers and pressed herself against him, her breasts brushing against his chest. She pulled away after a long moment, but kept her face near his, watching him slowly opening his eyes. "Wow," he whispered. "You're a-"

Karen cut him off by kissing him again. After her lips touched his for the first time she realized she couldn't get enough. She felt something within her ignite and she just had to kiss him one more time. Jack kissed her back immediately, opening his mouth to her prying tongue. She moaned against his lips, the sound almost startling her. She let her tongue tangle around his one more time before she pulled away again, stepping back completely.

"I was going to say," he smiled at her. "You're a _really_ good kisser."

Karen, coming back to herself, grinned slyly up at him and winked. "Thanks, honey. You too."

Jack, seemingly not at all phased, bounced around the closet, looking for more fun items to entertain himself with while Karen tried to calm her rapidly beating heart. He opened one of the drawers on the wall and found a few lighters and a deck of cards. With a dramatic gasp, Jack grabbed the cards and spun around to face Karen.

"Let's play strip poker!"

* * *

 **A/N: So the reason I had Karen dressed in the outfit we see her in during the strip poker scene is because I can't imagine she started out in anything more than what she had on. Also, she's probably pretty good at poker, especially when playing against Jack - which is why when we see them in the episode, Jack is only in his boxers and hat while Karen has her nightgown, boots, and coat. Either way, after a few more hands they would both be naked. Grace ruined it. xD**


	6. 23

**Season 5, Episode 23 - ' _23_ '**

Karen stood by the stairs, waving her goodbyes as her friends, _her family_ , walked out of the manse after Stan's funeral. It was getting late and she was exhausted from the craziness of the past few days. Between the divorce, Stan dying, and the panic of not knowing if she was even in the will she was ready to just lay back and sleep for days. The door closing brought her out of her thoughts and she watched as Jack turned to face her, a small smile on his face. Karen's stomach churned and she felt her face get hot with anger.

"Kare, I'm so excited about St. Barts!" he said with glee as he bounced towards her. He noticed the look on her face and he quickly became somber. "I'm sorry we are going under such sad circumstances, though." Karen said nothing, she only continued to stare at him, eyes blazing. Frowning, Jack stepped closer to her, placing a hand on her arm which she quickly slapped away. "Karen, are you okay?"

"Do I look like I'm okay?" she snapped, crossing her arms over her chest.

"Well actually," he said quietly, his voice wavering. "No, you look really mad-"

"I'm furious!" she exclaimed. "How could you?"

Jack stared at her, stunned. "What? What did I do?"

Karen let out a bitter laugh, rolling her eyes. "Do you think I'm stupid, Jack? I know you and Lorraine were all buddy-buddy at the funeral." She watched him open his mouth to speak up, but she cut him off, continuing. "Don't try to deny it. I watched you, I heard you." Tears sprang to her eyes, her first tears since finding out about Stan's death, and they weren't even for him. "You know, it was one thing when you first met Lorraine - it was an infatuation, I get that." She shook her head and felt the lump form in her throat. "But to realize that your best friend, someone you love so much, only loves you for your money... that's the worst feeling in the world."

"Karen," Jack scoffed. "You only loved Stanley for his money. Hell, you ended the funeral just to make sure you were still rich!"

The slap she hit him with echoed in the foyer where they stood. He was stunned into silence, a hand reaching up to cover his stinging cheek.

"How dare you," she growled at him, her voice low. "I loved Stanley! You don't know anything about my relationship with him." She clenched her fists by her side, her chest heaving with uneven breaths. "When I first met him, he was married and poor, but I loved him. I waited _ten years_ to be with him!" she yelled. "I may be materialistic and selfish, but I have always loved that man and I always will!" She shook her head disdainfully at him as Jack stared on in silence. "And not only do I have to deal with the fact that the man I loved for the past seventeen years is now gone forever, but then I find out that my best friend stabbed me in the back?"

"But I'm not with Lorraine, I'm with you."

"Yeah," she nodded her head, crossing her arms back over her chest and raising her chin in defiance. "After you found out that I got everything."

"Karen-"

"Get out."

Jack's eyes widened, his mouth opening and closing, not sure what to say. "But-"

"Get out!" She screamed at him and pointed towards the door.

Jack ran out of the manse as fast as he could, his face red and his eyes filling with tears at the realization that he just lost his best friend.

* * *

Later that evening, after taking a relaxing bath and packing her things for St. Barts, Karen sat on the bed of the guest room. She couldn't step foot into the master bedroom she shared with Stan. The memories were too painful, knowing the last woman he slept with in there was not her. She massaged lotion into her hands and stared at the ground, her mind drifting back to Lorraine's awful words from this afternoon.

 _"Too bad about your Jackie," the British woman said as she opened the door to exit the manse for the final time._

 _Karen frowned, her eyebrows knit together. "Why do you say that?"_

 _Lorraine turned to Karen, a devious smirk on her foul mouth. "I just thought you'd be upset to find out that your little 'Poodle' only hangs around you for your money, that's all."_

 _At that, Karen scoffed, rolling her eyes. "Listen, I know what you're trying to do." She placed her hands on her hips and raised her eyebrows. "And it's not going to work. My Jackie loves me."_

 _"Oh really?" Lorraine challenged. "Then why was he all ready to shove off with me the second he found out you might be penniless by the end of the day?"_

 _Karen sputtered, at a complete loss for words to which Lorraine laughed at before bidding her farewell and walking out the door._

Karen went over the events of the day in her mind and remembered Jack suddenly disappearing after she told him about the will and then the whispered hushes behind her from where Lorraine sat. There was also Jack holding her hand when Will was about to reveal the remaining of Stan's estate, but Jack was halfway in the aisle as well, leaning towards the British slut. Then there was the confrontation in the entryway where Jack didn't deny any of it. That was the final nail in the coffin.

She sighed, shaking her head and she leaned back against the soft pillows of the bed, her vision blurred as she stared at the ceiling. There was a quiet knock on her door, but she didn't move or say a word, wanting to be left alone. The door creaked open and someone entered the room making Karen annoyed and frustrated. She sat up and turned her body to yell at whoever dare bother her, but her breath caught in her throat when she saw Jack walking towards her. His face was blotchy and his eyes were bloodshot from his tears.

"Karen," he croaked out, his voice hoarse. "I know you hate me and I know you think I only love you for your money-" Her scoffing made him pause and he looked down at his feet in shame. "But you have to know that it's not true."

"Please," she cut in, standing from the bed to face him. "Spare me the lies, Jack."

He flinched when she said his proper name. She usually called him 'Jackie', 'Poodle', or 'Honey', only calling him 'Jack' when she was really upset or angry. "Okay, you want to know the truth?" he asked, looking up at her. Karen raised her eyebrow and cleared her throat, nodding her head at him to continue. "The truth is - _yes_ , I did suddenly want to become friends with Lorraine when I found out you might lose everything. I, too, am materialistic and selfish, Kare. Big surprise!" He gestured wildly about himself and rolled his eyes. "But that didn't mean I wasn't going to stop loving you or being around you-"

"That's not the point, Jack!" she shouted, throwing her hands up in the air. "You betrayed me the same way Stanley did!"

Jack looked horrified. "I didn't sleep with her!" he exclaimed, a hand pressed to his chest.

"No, but you _cheated_!" Karen yelled back. Angry tears began to fall from her eyes. "The two most important men in my life both cheated on me! Do you know how that makes me feel? I have never kept a secret from you, you know more about me than Stan did at times!" A sob escaped her and she pressed her hand to her forehead, trying to control herself, and then looked back at him again. "I can't even keep the attention of a gay man..." she laughed bitterly. "I'm worthless."

"Karen, don't say that," Jack whispered, his own tears threatening to fall. He stepped towards her, but still kept his distance, the memory of her slapping him this afternoon still fresh in his mind. "You are the most important person in my life-"

"Only because I buy you things," she muttered.

Jack felt his own anger rise within him and he snapped. "Damn it, Karen, can you please stop interrupting me for five _goddamn_ seconds?!"

Karen gaped at him, never being to spoken like that by him before, but she said nothing more. Taking her silence as a clue to continue, Jack spoke again, his voice more calm.

"You know when we first met, I tried everything in my power to not get attached to you. I didn't want a hag and I especially didn't want to become Will and Grace." He closed the distance between them, no longer fearing the strike of her hand, and he tilted her face up to his with his finger under her chin. "But I couldn't keep myself away from you," he smiled, his eyes boring into hers deeply. "You wormed your way so quick right into my heart, Karen. I was terrified by how much I loved you. I even picked a stupid fight with you after divorcing Rosario because I was so scared. But I eventually accepted it because I realized that you make me so happy, Karen. And it's not the kind of happiness I get when you buy me things." He moved his hand down and placed his palm on her chest over her heart. "It's the happiness from being so purely loved by an amazing woman."

Karen had trails of tears running down her cheeks, her control over her emotions completely shot to hell at this point. "Do you really love me, Jackie?"

He sighed in relief at her use of his nickname. He wrapped her in his arms and kissed her forehead. "I love you so much, Karen," he whispered into her hair. "I'm so sorry."

They didn't speak for a few minutes, content with just holding each other. Karen kept her arms tight around his waist, her face pressed against his shoulder while Jack had his nose buried in her neck, his hands rubbing her back soothingly. He heard her mumble something, but it was muffled by the material of his shirt.

"What?" he asked.

Karen lifted her head and smiled warmly at him. "You came back to me," she repeated. At Jack's look of confusion, she elaborated. "When I left Stan, I wanted nothing more than for him to come back to me. I wanted him to fight for me, prove to me that he loved me," she explained. "I kicked you out earlier and it only took you a few hours to come back."

A grin broke out onto Jack's face and he leaned down to press his forehead against hers. "I told you, you stole my heart the first day we met. And nothing can ever change that."


	7. FYI: I Hurt, Too

**Season 7, Episode 1 - FYI: I Hurt, Too**

Jack entered his apartment and dropped his luggage by the doorway, a sigh of relief escaping his lips. It was 2 am and he was exhausted, finally arriving home from his three month tour with J-Lo. He closed and locked the door behind him, shuffling his feet towards his bedroom. His eyes were barely open, his body and mind completely sleep deprived. He kicked off his shoes and tore off his jean jacket, dropping it to the floor next to the couch. He pulled his shirt over his head and unbuckled his pants, shoving them down his legs, almost tripping over them as he entered his bedroom. He moved towards the bed, but stopped suddenly, a frown forming on his tired face.

Someone was in his bed.

He squinted in the darkness and felt a smile break out on his face when he recognized the form lying under the covers. He climbed on to the bed and slid under the covers, wrapping an arm around her shoulders and pulling her to his chest. Her eyes fluttered open and she pouted. He could see her confusion at being woken up, but then it turned into glee.

"Poodle," she whispered. She wrapped her arms around his back and pressed her nose to his neck, taking in his familiar scent.

Jack rest his lips against her forehead, pressing a few kisses there while he held her tighter to him. "I'm sorry about Lyle."

Karen sighed, the expulsion of warm breath on his chest causing him to shiver. "Yeah, me too."

Jack was quiet for a moment, his fingers playing with her hair. He had so much he wanted to tell her about his experience on tour, but he first and foremost needed to make sure she was okay since he completely ditched her at her wedding reception after she announced her divorce. He felt even worse when she constantly called him while he was gone, but he was never able to talk - either busy with rehearsal, the performance, or schmoozing with Jennifer Lopez. Eventually she stopped calling and yet there she was, in his bed the night he came home. "I shouldn't have left you."

Karen pulled her head back from his neck to look up at him. "What?"

Jack gazed into her hazel eyes, his face only inches from hers. "I left you, blew you off when you needed me-"

"Jackie," she moved her hand to his face, her thumb grazing the stubble on his chin. "You had an amazing chance to work with one of the biggest stars in the world. Did you really think I was going to let you give that up?" He didn't say anything and her frown deepened. "Is that why you left so fast?"

He nodded, the movement causing his nose to brush hers. "I didn't want to see you hurting because I knew the second I saw how upset you were, I wouldn't have gone anywhere." He let out a humorless chuckle. "Hence my 'dramatic moment' with you."

Despite herself, Karen smiled. "I'm glad you went, Poodle. There was no one in the world more deserving. And I'm fine, I promise." He eyed her and she sighed, knowing he saw right through her. "Well, I will be fine... eventually."

Jack closed the tiny gap between them and kissed her tenderly. "I'm here now," he said when he pulled back, his lips still brushing hers as he spoke. "Promise you'll talk to me if you need to?"

She grinned, tracing his lips with her finger. "I promise."

Jack pressed a kiss to her finger and then her forehead. "Goodnight, Bear. I love you."

Karen buried her nose back into his neck and their eyes drifted closed, giving in to sleep. "Love you," she whispered.


	8. The Kids Stay Out of the Picture

**Season 5, Episode 3 - _The Kids Stay Out of the Picture_**

After getting yelled at by Will and Grace, Jack and Karen left and went across the hall to his apartment. Karen pouted as she sat on the blue couch, Jack following behind her.

Noticing the expression on her face, Jack frowned. "What's the matter, Kare?"

Karen huffed and crossed her arms over her chest petulantly. "I didn't get to finish showing you how Leo kissed," she grumbled, her eyebrows furrowed.

"Aww," Jack deflated and a pout formed on his lips as well, disappointed. "Wait!" He perked up and laid a hand on Karen's arm, drawing her attention to him. "Just show me again! He's already good - how much better could he be?"

"Oh honey," Karen fanned herself again.

"Well show me, show me!" He was bouncing in his seat in excitement.

Karen didn't dawdle - she grabbed his face in her hands and brought her lips to his, pouring everything into the kiss. It was hard, deep, passionate, and exhilarating. She tilted her head and brushed her tongue over his lips teasingly and after a good, full minute, she pulled away, their mouths parting with a smack.

When she opened her eyes she saw the same dazed look she had on her own face a few days ago when Grace kissed her reflected on Jack's features. Jack kept his gaze on her lips as they lightly panted together, Karen's hands still cradling his face. Like magnets, they collided again. Her tongue immediately slid into his mouth to seek his out. Jack wrapped his arms around her, pulling her on to him so she was straddling him on the couch. Karen's arms went around his neck and she grinded down into his lap, surprised to feel a slight buldge between her legs. Jack grunted and grabbed her ass in his hands pulling her impossibly closer. He bucked his hips up and she whimpered against his mouth, tugging the hair at the back his neck. Karen moved against him again, rubbing herself through his jeans and her slacks. She didn't know what was happening or what came over them, but she never had such a carnal desire to fuck her best friend before now. She moaned when Jack used his hands on her ass to guide her as he raised up, increasing the friction between their bodies.

Karen came quick, but hard, her thighs quaking from the sensation. She gasped into Jack's mouth, holding his chin in her hand as they breathed into each other's mouths, hazel eyes boring into light blue. She saw the desperation on his face and began to jerk her hips back and forth again, her pelvis snapping into his. She shoved her tongue back in his mouth as he finally came, his cock twitching in his tight jeans and his fingers digging into her ass cheeks, a guttural moan of pleasure vibrating against their lips.

They stared at each other, the realization of what just transpired between them hitting like a ton of bricks. Karen slid off from his lap and on to the couch beside him, her eyes glancing down at the dark spot on his jeans. Jack grabbed a nearby pillow and placed it over his lap, but it was a moot point to which Karen couldn't help but let out a giggle. He stared at her for a moment before erupting into laughter himself.

"Sorry," Karen said after they calmed.

"For what?" Jack asked, tilting his head to the side like a confused puppy.

Karen smiled and reached over to wipe a smear of lipstick off his bottom lip, cupping his jaw in her hand. "For what just happened... I didn't mean to take advantage of you-"

"You didn't take advantage of me," he cut her off with a shake of his head and grabbed her hand from his face, holding it in his lap. "I'm sure Leo is a great kisser." He leaned over, kissing her cheek, and whispered in her ear. "But no one compares to you."

Karen shivered as his lips brushed her ear and as he stood from the couch she stared up at him quizzically, but decided not to question him. Jack walked to the bedroom and looked over his shoulder as he spoke. "I'm gonna change my uhhh well my pants and underwear," he grimaced and Karen blushed. "You wanna have a sleepover?"

Karen cleared her throat and stood from the couch, grabbing her purse that she left there earlier. "No, honey," she replied with a timid smile. "I think I'll head home-"

They heard the door across the hall slam, the sound almost making the walls rattle and they stared at each other in surprise. Jack quickly changed his clothes while Karen ran out into the hall to find Grace smashing the elevator button, tears streaming down her face.

"Gracie?" she asked quietly as she walked up to the distraught woman. "What happened?"

"I don't want to talk about it," Grace sobbed, wiping tears away from her face. The elevator dinged open and the red head rushed inside just as Jack exited his apartment with a fresh pair of pants on and a confused expression on his face.

"Is everything okay?" he asked, glancing at 9C before turning his attention to Grace inside the elevator.

Karen opened her mouth to respond when the elevator dinged again and the doors started to close. "I- wait, Grace!"

But the doors slid shut in front of her face and Karen sighed, looking over at Jack with worry.

"What the hell is going on?"


	9. Back Up, Dancer

**Season 7, Episode 2: " _Back Up Dancer_ "**

" _Oh, to answer your question - Madonna_ ," Jack said and Karen sighed against him, dropping her hand from his shoulder. He looked down at her in confusion, wondering why she stopped moving with him. "What?"

Karen rolled her eyes. "You are so sweet, but such an ass at the same time," she told him. Jack pouted and Karen let a smile break out on to her face as she slipped her hand from his and wrapped her arms around his neck. Jack casually slid his hands down to her lower back and Karen pressed herself against him as they began to sway again. "This would be easier with music," she said.

Jack leaned down, pressing his lips to her ear and he began to hum a tune. Karen breathed out in content and closed her eyes as they continued their little dance. Her fingers reached up and she tangled them gently in the hair at the back of his neck causing him to shiver. She turned her face towards his neck and pressed the tiniest of kisses against his warm skin. She tilted her face and placed another kiss below his ear and then worked her way to his jaw. Jack turned his head and captured her traveling lips between his. He ran his tongue slowly back and forth over her lips and then pulled away, their lips parting with a light smack. Karen caught his upper lip and then opened her mouth just as Jack did his and their tongues brushed, twisting together in a slow dance, a sigh escaping between their mouths.

Karen unwrapped one arm from around his shoulders and traced his jaw down to his chin with her fingernail gently. She tilted her head at a different angle and moaned at the lackadaisically paced passionate kiss. Placing her palm against his cheek, Karen pulled away for a quick breath only to have Jack seize her lips again.

He took a few steps forward, guiding Karen until her back came into contact with the wall and he molded their bodies together, his thigh between her legs. Their movements weren't rushed, they kept their kisses lazy. His hands moved from her lower back to her stomach, his fingers sliding under the loose material of her shirt to graze against her skin. Karen mewled into his mouth and Jack smirked against her lips. His hands slid up further and his thumbs pushed up on her bra so he could brush the underside of her breasts.

Karen moved her hands down from his face and pressed them against his pecs, appreciating the feel of his strong muscles beneath his shirt. Just as Jack's fingers slid further inside her bra, his cell phone began to ring loudly in his pocket and their lips parted with a ' _pop_ '. He rest his forehead against hers and removed his hands from under her shirt, one resting on her waist while the other dug in the pocket of his sweatpants to find his phone.

He fished it out and flipped it open, pressing the device to his ear. "Hello?" he asked breathlessly. "Oh, hey Will..."

Karen rolled her eyes, hearing Will's yammering on the other line. She slanted her head and continued to pepper his chin and jaw with kisses as he chatted with their lawyer friend.

"Yeah, Karen is here with me. Dessert? All right, we'll head over. Okay, bye." He hung up the phone and Karen pulled away to stare up at him. "Will, Grace, and Vince are having drinks and dessert."

"She has the wedding album out, doesn't she?" Karen asked with a sigh as Jack stepped back from her.

"Probably," he shrugged. He walked over and grabbed his duffle bag as Karen picked up her purse off the table. "Kinda pathetic, ain't it?"

"I don't think it's pathetic."

Her voice was small and Jack turned to look at her as she fiddled with the strap of her purse. "Sorry, Kare," he mumbled. "I forgot-"

"Its okay, honey." She plastered on a smile that he knew was partially fake and reached her hand out for him to take.

Jack slid his hand in hers and squeezed, planting a kiss on her cheek as they walked out of the dance studio.


	10. Forbidden Fruit

**Season 8, Episode 12 - " _Forbidden Fruit_ "**

He heard the voices, quiet, but harsh and slightly raised. Jack peered his eyes open, letting them adjust to the darkness of the room and settled on the slightly open library doors. A sliver of light streamed into the room, the small form of an angry Karen revealed and a large shadow cast upon her, obviously Stanley. He listened intently, trying to understand what they were arguing about.

"Damn it, Stanley!" she growled. "I will not have this argument with you again!"

"He's an adult, Karen!" Stan said back and Jack blushed, realizing he was the subject of their current disagreement. "I'm only home for a few days and you're spending all your time with him!"

"He's sick, goddamnit. I'm not leaving him be!"

"Why not?"

"He needs someone to take care of him, Stan." She sounded tired and he could just barely make out her covering her face with her hands.

"And why should that someone be you?" Stan still sounded annoyed, almost borderline pissed. "He lives across the hall from Will and Grace, I'm sure one of them could help out. You always do this. The second he calls you drop everything in your life and go to him."

"Stan..."

"Don't try to deny it, Kare. You know it's true."

Jack watched Karen cross her arms over her chest, her mouth set in a tight line and a firm glare fixed on her husband. "What do you want from me, Stanley?"

Jack swallowed loudly and heard Stan sigh in exasperation.

"You're my wife, Karen."

"My being married to you has nothing to do with my relationship with Jack."

"It has everything to do with it!" he bellowed at her.

"Sssh!" Karen shrieked. "You'll wake him up!"

"I don't care!" the large man continued to shout. "Why do you do it, Karen?"

"He needs me."

"He survived his first 29 years without you. He does not need you for anything."

"Stan-"

"Why can't you just tell me, Karen?"

"It doesn't matter why-"

"Karen!"

"Because I need him!" she screamed.

Jack muffled his gasp behind his blanket. It was silent for a long few moments and he held his breath in anticipation for the words that were to be spoken next.

"You need him?" Stan asked finally, his voice much quieter than before. "You've never needed anyone before. You thrive on your independence. What is this really about?"

Another silence enveloped them and Jack watched Karen's face intently, seeing her eyes flicker between Stan the door to her left. The Forbidden Room.

"Karen..." His tone was understanding and soft which confused Jack. He learned what was behind that door earlier this afternoon, but what did it have to do with him? "You can't keep doing this to yourself."

"I'm not doing anything, honey." Her voice was small and wavered slightly. "I haven't thought about that room in years, honestly. But Jackie..." she trailed off and Jack bit his lip in curiosity. "He's like the son I never had."

"But Mason-"

"Yes, Mason is my stepson and I love him, I do. Olivia too." She reached out and grabbed his large hands in hers. "But Jackie and I clicked right away, we had a special bond from day one. He's the best friend I've ever had. And for two years, honey, he was the most important man in my life..." She paused for a moment and looked down at her shoes. Jack could tell she was hesitating telling him something and his mind raced. "Honestly, I think he still is."

"What's that supposed to mean?"

There was a beat and he saw Karen open her mouth to respond, but Jack coughed unexpectedly. He panicked, seeing Karen snap her head toward the direction of the library doors and he closed his eyes, pretending to be asleep. A few more coughs escaped him and he cleared his throat, pulling the covers higher up over his shoulders as he shuddered.

"Go to bed, Stan," Karen said quietly. "We'll talk in the morning." She didn't wait for a response and Jack tried to settle his breathing as he heard Karen shuffle into the room. He felt her sit beside his shoulder, her hand gliding over his forehead before it settled on his cheek. He continued to pretend to be asleep until he heard a sniffle and something wet fall onto his cheek. He fluttered his eyes open and saw Karen's head bowed, her other hand pressed to her nose as she silently cried.

"Kare," he croaked out, his voice still sore.

She gasped and wiped at her eyes frantically, trying to cover up the fact that she was crying even though he obviously saw it. "Poodle," she whispered. "How are you feeling?"

He sat up and her hand fell to his chest, her warm fingers sliding beneath the blue pajama shirt he wore. "Why are you crying?"

"I'm not crying."

He gave her a look and reached up, swiping his thumb under her eye, gathering a stray tear. "You were saying?"

She grabbed his hand from her face and kissed his palm before bringing it to her lap and placing her other hand on top of his. "I don't really know why I'm crying, honey," she confessed. "Its been a strange day."

"I'm sorry, again, for making you tell me about that room."

"I told you its okay-"

"But you're upset and I hate that I made you upset."

"You didn't make me upset, baby," she assured him, a warm smile on her lips. She maneuvered herself more onto chaise, pulling Jack's face to her bosom and wrapped her arms around him, her chin resting atop his head. Jack draped his arm over her waist and pulled her closer, hooking his ankle with hers to keep her in place. They sighed in content, their bodies relaxing in each others embrace.

"Hey Kare?"

"Hmm?"

"Who's your daddy?" He felt her giggled against him and it warmed his heart.

"You are." She pressed her lips to his forehead and kept them there for a while. "Your fever has gone down," she mumbled.

"Thank you for taking care of me."

"Its no problem, honey." She lifted her chin and pressed a kiss to the top of his head before resting her cheek there. "Now let's get some sleep, Poodle."

He snuggled further into her chest and they settled down for sleep, their breaths beginning to even out. Before succumbing to sleep, Jack mumbled drowsily into her neck.

"You'd be an amazing mom, Karebear."


End file.
